1

Supporting Information

Rec. Nat. Prod. 14:1 (2020) 57-64

Two Novel Sesquiterpenes and A New Pregnane Derivative from

the South China Sea Gorgonian Subergorgia suberosa

Xian-Qiang Chen 1, 2, Nannan Xing3, Bin Yang 2, Xuefeng Zhou 2, Chenghai

Gao 1 and Yonghong Liu 1, 2

1 Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning, Guangxi 530200,

P. R. China 2 Key Laboratory of Marine Bio-resources Sustainable Utilization; Guangdong Key Laboratory

of Marine Materia Medica; Research Center for Marine Microbes, South China Sea Institute of

Oceanology, Chinese Academy of Sciences, Guangzhou, Guangdong 510301, P. R. China 3 Guangxi Key Laboratory of Chinese Medicine Foundation Research, Guangxi Scientific

Experimental Center of Traditional Chinese Medicine, Guangxi University of Chinese Medicine,

Nanning, Guangxi 530200, P. R. China

Table of Contents Page

Figure S1: HR-ESI-MS Spectrum of 1 (isosuberosenol A) 3

Figure S2: 1H-NMR (500 MHz, CDCl3) Spectrum of 1 (isosuberosenol A) 4

Figure S3: 13C-NMR (125 MHz, CDCl3) Spectrum of 1 (isosuberosenol A) 5

Figure S4: DEPT135 (125 MHz, CDCl3) Spectrum of 1 (isosuberosenol A) 6

Figure S5: HSQC Spectrum of 1 (isosuberosenol A) 7

Figure S6: HSQC Spectrum of 1 (isosuberosenol A) (From δC15 ppm to δC 35 ppm) 8

Figure S7: HMBC Spectrum of 1 (isosuberosenol A) 9

Figure S8: HMBC Spectrum of 1 (isosuberosenol A) (From δC 79 ppm to δC 85 ppm ) 10

Figure S9: HMBC Spectrum of 1 (isosuberosenol A) (From δC 38 ppm to δC 53 ppm ) 11

Figure S10: HMBC Spectrum of 1 (isosuberosenol A) (From δC 15 ppm to δC 36 ppm ) 12

Figure S11: 1H-1H COSY Spectrum of 1 (isosuberosenol A) 13

Figure S12: NOESY Spectrum of 1 (isosuberosenol A) 14

Figure S13: HR-ESI-MS Spectrum of 2 (suberosain A) 15

Figure S14: 1H-NMR (500 MHz, CDCl3) Spectrum of 2 (suberosain A) 16

Figure S15: 13C-NMR (125 MHz, CDCl3) Spectrum of 2 (suberosain A) 17

Figure S16: DEPT135 (125 MHz, CDCl3) Spectrum of 2 (suberosain A) 18

Figure S17: HSQC Spectrum of 2 (suberosain A) 19

Figure S18: HSQC Spectrum of 2 (suberosain A) (From δC 14 ppm to 50 ppm) 20

Figure S19: HMBC Spectrum of 2 (suberosain A) 21

Figure S20: HMBC Spectrum of 2 (suberosain A) (From δC 52 ppm to 75 ppm) 22

Figure S21: HMBC Spectrum of 2 (suberosain A) (From δC 15 ppm to 50 ppm) 23

Figure S22: 1H-1H COSY Spectrum of 2 (suberosain A) 24

Figure S23: NOESY Spectrum of 2 (suberosain A) 25

Figure S24: HR-ESI-MS Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) 26

Figure S25: 1H-NMR (500 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3,

20-dione)

27

2

Figure S26: 13C-NMR (125 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3,

20-dione)

28

Figure S27: DEPT135 (125 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3,

20-dione)

29

Figure S28: HSQC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) 30

Figure S29: HSQC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 12

to 42)

31

Figure S30: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) 32

Figure S31: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 42

to 70)

33

Figure S32: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 12

to 40)

34

Figure S33: 1H-1H COSY Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) 35

Figure S34: NOESY Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) 36

3

Figure S1: HR-ESI-MS Spectrum of 1 (isosuberosenol A)

4

Figure S2: 1H-NMR (500 MHz, CDCl3) Spectrum of 1 (isosuberosenol A)

5

Figure S3: 13C-NMR (125 MHz, CDCl3) Spectrum of 1 (isosuberosenol A)

6

Figure S4: DEPT135 (125 MHz, CDCl3) Spectrum of 1 (isosuberosenol A)

7

Figure S5: HSQC Spectrum of 1 (isosuberosenol A)

H4/C4

H3a/C3

H2/C2

H3b/C3

H11/C11

H12a/C12

H12b/C12

8

Figure S6: HSQC Spectrum of 1 (isosuberosenol A) (From δC15 ppm to δC 35 ppm)

H6/C6

H10a/C10

H10b/C10 H9a/C9 H9b/C9

H15/C15

H7/C7

H14/C14 H8/C8

9

Figure S7: HMBC Spectrum of 1 (isosuberosenol A)

10

Figure S8: HMBC Spectrum of 1 (isosuberosenol A) (From δC 79 ppm to δC 85 ppm )

H2/C4

H12a/C4

H3b/C4 H12b/C4 H6/C4 H6/C4

H4/C1

H3a/C1

H2/C1 H8/C1 H12b/C1

H7/C1 H6/C1

11

Figure S9: HMBC Spectrum of 1 (isosuberosenol A) (From δC 38 ppm to δC 53 ppm )

H14/C12 H6/C12 H15/C12

H12b/C5 H12a/C5 H8/C5

H2/C5 H3a/C5

H12b/C5

H6/C5

H14/C11 H15/C11

H9b/C11 H10b/C11

H10a/C11

H10b/C2

H10a/C2

H3b/C11

H3b/C2 H3a/C2

H3a/C11

H8/C2

H2/C11

12

Figure S10: HMBC Spectrum of 1 (isosuberosenol A) (From δC 15 ppm to δC 36 ppm )

H14/C15 H12b/C15 H12a/C15

H14/C13 H15/C13 H12b/C13 H12a/C13 H2/C13

H15/C14

H7/C8 H12a/C14

H7/C9 H8/C9

H9a/C10 H8/C10

H9a/C7 H8/C7

H12a/C6 H12b/C6

13

Figure S11: 1H-1H COSY Spectrum of 1 (isosuberosenol A)

14

Figure S12: NOESY Spectrum of 1 (isosuberosenol A)

15

Figure S13: HR-ESI-MS Spectrum of 2 (suberosain A)

16

Figure S14: 1H-NMR (500 MHz, CDCl3) Spectrum of 2 (suberosain A)

17

Figure S15: 13C-NMR (125 MHz, CDCl3) Spectrum of 2 (suberosain A)

18

Figure S16: DEPT135 (125 MHz, CDCl3) Spectrum of 2 (suberosain A)

19

Figure S17: HSQC Spectrum of 2 (suberosain A)

H16a/C16 H16b/C16

H6a/C6 H6b/C6

H-OMe/C-OMe

H5/C5 H11/C11

H2/C2

20

Figure S18: HSQC Spectrum of 2 (suberosain A) (From δC 14 ppm to 50 ppm)

H12a/C12

H12/C12

H8/C8

H15/C15

H10/C10 H14/C14

H7/C7

21

Figure S19: HMBC Spectrum of 2 (suberosain A)

H16a/C4 H16b/C4

H6a/C4 H6b/C4

H5/C4

H16a/C3

H16a/C2 H16b/C2

22

Figure S20: HMBC Spectrum of 2 (suberosain A) (From δC 52 ppm to 75 ppm)

H5/C6

H-OMe/C6

H6a/C-OMe

H6b/C-OMe

H6a/C5

H6a/C1

H6b/C5

H6b/C1 H8/C1

H9a/C1

H11/C1

H5/C1 H8/C5 H12a/C5

H12a/C1

H12b/C5

H12b/C1

H7/C1

23

Figure S21: HMBC Spectrum of 2 (suberosain A) (From δC 15 ppm to 50 ppm)

H14/C11

H12a/C2

H12b/C2 H15/C11

H14/C12 H15/C12

H5/C12 H14/C13 H15/C13 H12a/C13 H12b/C13

H12a/C8 H12b/C8 H7/C8 H5/C8

H12a/C14

H12b/C15 H14/C15

H7/C9

H15/C14 H12b/C14

H12a/C15

H8/C9

H8/C10 H9a/C10

H8/C7

H11/C10 H11/C9

24

Figure S22: 1H-1H COSY Spectrum of 2 (suberosain A)

25

Figure S23: NOESY Spectrum of 2 (suberosain A)

26

Figure S24: HR-ESI-MS Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

27

Figure S25: 1H-NMR (500 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

28

Figure S26: 13C-NMR (125 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

29

Figure S27: DEPT135 (125 MHz, CDCl3) Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

30

Figure S28: HSQC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

H17/C17

H22a/C22 H22b/C22

H14/C14

H4/C4 H5/C5

H9/C9

31

Figure S29: HSQC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 12 to 42)

H12/C12

H2a/C2 H2b/C2 H1a/C1

H1a/C1

H8/C8

H11a/C11 H11b/C11

H6/C6

H19/C19

H16/C16

H15/C15

H7a/C7

H7b/C7

H18/C18

32

Figure S30: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

H1b/C3 H1a/C3 H2a/C3

H2b/C3 H21/C20 H17/C20 H22b/C3

33

Figure S31: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 42 to 70)

H18/C17 H12/C17 H16/C17 H21/C17

H18/C14

H2b/C4 H5/C4

H19/C5 H1a/C5

H18/C13

H8/C13 H16/C13

H19/C9 H7b/C9

H1b/C9

H12/C9

H5/C9 H11a/C9

H1a/C9

H17/C13

34

Figure S32: HMBC Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione) (From δC 12 to 40)

H18/C12

H17/C12

H19/C1

H19/C10

H1b/C2 H1a/C2 H2a/C1 H9/C1

H9/C11

H1b/C10 H9/C10

H5/C10 H1a/C10 H2b/C10 H2a/C10

H5/C6

H1b/C19 H9/C19

H14/C15

H14/C16

H16/C15 H17/C16 H17/C15

H17/C18 H12/C18

H9/C8 H7b/C8 H7a/C8

35

Figure S33: 1H-1H COSY Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)

36

Figure S34: NOESY Spectrum of 3 (4-hydroxymethyl-5β-pregnan-3, 20-dione)